by Terrance Ellis | Dec 24, 2025 | Uncategorized
This is a senior, hands-on technical leadership role where you’ll set the technical vision for Virtual Care and build systems that directly increase clinical capacity. If you’re a Ruby on Rails expert who can architect at scale, ship pragmatically, and still keep the codebase clean, Fabric Health is built for you.
About Fabric Health
Fabric Health is powering boundless care by solving healthcare’s biggest constraint: clinical capacity. They unify the care journey from intake to treatment with intelligent automation that removes admin burden and helps care delivery run 2–10x more efficiently. Trusted by major health systems and backed by top investors, Fabric builds fast, high-quality products that keep patients and providers moving.
Schedule
- Full-time, remote (United States)
- Cross-functional collaboration with product, design, and clinical experts
- High-ownership role with strategic influence and hands-on execution
What You’ll Do
⦁ Lead the Virtual Care team’s technical vision and set architectural direction for speed, efficiency, and quality
⦁ Architect and develop Fabric’s core Ruby on Rails backend with strong performance, scalability, and security
⦁ Act as a technical authority, raising code quality, best practices, and engineering standards through hands-on guidance
⦁ Build and evolve the React front end to create intuitive experiences for providers and patients
⦁ Translate complex clinical and product requirements into elegant, well-documented technical solutions
⦁ Drive adoption of new technologies and methods to improve delivery, reliability, and developer velocity
⦁ Contribute to the long-term roadmap and help define the future of Fabric’s virtual care platform
What You Need
⦁ 8+ years of full-stack web development experience on cross-functional agile teams
⦁ Deep, demonstrable expertise in Ruby on Rails
⦁ Experience with React or a modern JavaScript framework
⦁ Proven ability to design, build, test, secure, and document production systems
⦁ Strong technical leadership through influence, mentoring, and architecture (not people management)
⦁ Comfort driving ambiguous initiatives from “why” to shipped systems
⦁ Familiarity with healthcare industry challenges and motivation to solve them with technology
Benefits
⦁ Salary range: $160,000–$200,000 per year
⦁ Medical, dental, and vision insurance (role-eligible)
⦁ Unlimited PTO (role-eligible)
⦁ 401(k) plan (role-eligible)
⦁ Potential additional compensation such as stock options and bonuses (role-eligible)
If you want your architecture to matter in the real world, this is one of those rare roles where it actually does. Apply while it’s open.
Build the platform that helps care teams move faster and patients get help sooner.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 24, 2025 | Uncategorized
This is a high-leverage backend seat where you’ll shape the systems powering fantasy sports and DFS for millions of users. If you like building fast, reliable, real-time infrastructure and you want real ownership, Sleeper is handing you the keys.
About Sleeper
Sleeper connects people over sports through games and community, spanning fantasy leagues, pick’em contests, and real-time interactions with friends. They run lean on purpose so each engineer has meaningful impact, and they’re backed by top-tier Silicon Valley investors. The focus is simple: delightful user experience built on performance, scalability, and reliability.
Schedule
- Full-time, remote-friendly (United States)
- Location preference: SF Bay Area, Los Angeles, NYC, or Pacific Northwest
- Flexible remote work policy (collaboration across teams expected)
What You’ll Do
⦁ Design and build core backend systems powering Sleeper’s games and real-time experiences (fantasy contests, Sleeper Picks, profiles, leaderboards, and more)
⦁ Architect scalable distributed services that support millions of concurrent users with low latency and high availability
⦁ Lead backend initiatives end-to-end, from concept through deployment, with clean interfaces and well-documented services
⦁ Improve performance through monitoring, profiling, and capacity planning, proactively removing bottlenecks
⦁ Partner with product, design, and frontend teams to ship features users love
⦁ Mentor engineers through code reviews, technical guidance, and raising backend best practices
⦁ Drive technical direction and contribute to engineering culture as a senior leadership voice
What You Need
⦁ 7+ years of backend engineering experience, including staff-level or tech lead ownership
⦁ Strong track record designing and scaling distributed systems for real-time, gaming, or high-traffic environments
⦁ Proficiency in one or more backend languages (Go, Python, Node.js, Java, or similar) and sound judgment on trade-offs
⦁ Deep database knowledge (SQL + NoSQL), caching strategies, and message queues (Kafka, RabbitMQ, Pub/Sub, etc.)
⦁ Experience designing and maintaining REST and/or GraphQL APIs, data models, and internal tooling
⦁ Cloud experience (AWS, GCP, or similar) and comfort with containers (Docker); Kubernetes is a plus
⦁ Product mindset and strong communication skills, with a consistent habit of mentoring and elevating teammates
⦁ Bonus: Interest in sports, gaming, or multiplayer/real-time systems
Benefits
⦁ Competitive salary: $225,000–$300,000/year (not inclusive of equity and benefits)
⦁ Equity
⦁ Medical, dental, and vision insurance
⦁ 401(k) with company matching
⦁ Generous PTO and flexible remote work policy
⦁ Fast growth opportunities on a small, focused team
Roles like this don’t come up often. If you want to own major backend decisions and ship to a massive user base, move now.
Build the backbone of a sports platform that actually feels alive.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 24, 2025 | Uncategorized
If you’re tired of building cute AI demos and want to ship real systems that touch revenue, safety, and compliance, this role is the real deal. You’ll help build Fleetworthy’s foundational AI platform, with massive datasets, board-level visibility, and production outcomes that actually matter.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and toll management command center built to simplify operations and reduce risk. In September 2024, Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze unified under the Fleetworthy name to deliver one connected suite for fleets and drivers.
Schedule
• Canada-based (remote or hybrid)
• Foundational role on a newly created AI platform team
• High-visibility work with executive and board-facing communication
What You’ll Do
⦁ Build and own core AI infrastructure: feature store, model CI/CD, evaluation harnesses, and observability across AI efforts
⦁ Write and ship production code daily using Python, Go, and TypeScript
⦁ Architect and scale core components of AI and data infrastructure
⦁ Implement AI into real business systems across tolls, documents, and devices at massive scale
⦁ Collaborate cross-functionally with product, design, compliance, and customer support
⦁ Set technical direction for other engineers, vendors, and contractors
⦁ Present roadmap, progress, and results directly to executives and the board
What You Need
⦁ 4+ years building backend or infrastructure systems, plus 2+ years production experience in AI/ML
⦁ Proven track record delivering AI applications (RAG, LangChain, MCP servers, or similar)
⦁ Experience with LLMs, computer vision, and/or real-time event processing
⦁ Strong system design and technical leadership skills
⦁ Bias toward shipping working software in ambiguous, fast-moving environments
⦁ Bonus: experience in logistics, tolling, transportation, or other regulated domains
Benefits
⦁ Work with a defensible data moat: 10+ years of toll, inspection, safety, and vehicle data across all 50 U.S. states
⦁ Build production AI that impacts safety, compliance, customer trust, and revenue
⦁ Modern stack: Python, Go, TypeScript, GCP/AWS, Postgres, Redis, Kafka, MLFlow, dbt, Dagster, LangChain, Triton Inference Server
⦁ Early seat on a platform transformation with real buy-in, budget, and ownership
If you’re qualified for this, don’t play small. These “foundational AI engineer” roles don’t sit open long.
If you want to own the backbone of a real AI platform and ship systems that move the business, this is your shot.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 24, 2025 | Uncategorized
If you like building the plumbing that makes data teams faster, safer, and more self-sufficient, this role is for you. You’ll help scale a modern data platform that supports Data Mesh, automation, and reliable data products across a growing fleet tech company.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and toll management command center built to simplify operations and reduce risk. In September 2024, Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze unified under the Fleetworthy name to deliver one connected suite for fleets and drivers.
Schedule
• Canada-based (remote or hybrid)
• Geographically distributed remote team
• Fast-paced environment supporting large, complex datasets and platform reliability
What You’ll Do
⦁ Build and maintain platform tools for deployment and automation of data products
⦁ Partner with value stream teams to adopt Data Mesh principles and scale team-owned data products
⦁ Design and optimize ingestion and transformation pipelines using SQL, Python, and PySpark
⦁ Apply infrastructure-as-code (Terraform or similar) to automate platform provisioning
⦁ Contribute to CI/CD workflows for data pipelines and platform services
⦁ Improve platform reliability, performance, and cost-efficiency at scale
⦁ Collaborate across a distributed team to strengthen platform standards and best practices
What You Need
⦁ Strong SQL, Python, and PySpark skills in data-intensive environments
⦁ Solid understanding of ETL, Medallion Architecture, data modeling, and data warehousing
⦁ Strong communication skills and comfort working in a remote, distributed team
⦁ A builder mindset: curious, proactive, and eager to learn platform and infrastructure practices
⦁ Collaborative approach, focused on enabling other teams to deliver high-quality data products
Benefits
⦁ Remote or hybrid flexibility in Canada
⦁ Work on a modern data platform supporting Data Mesh architecture
⦁ High-impact role improving automation, reliability, and scalable data delivery
This is a great role for someone who wants to level up from “data pipelines” to “data platform.”
If you’re ready to build systems that let teams ship clean data products faster, step up and apply.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 23, 2025 | Uncategorized
Two sentences that grab attention and tell remote job seekers why this role matters.
Prompt needs a Support Engineer who can live in the middle of customers and code, turning messy production problems into clean fixes and clear specs. If you like debugging, digging through logs, writing queries, and translating chaos for engineers and stakeholders, this role is your lane.
About Prompt Therapy Solutions, Inc.
Prompt builds highly automated, modern B2B software for rehab therapy businesses, their teams, and the patients they serve. They’re scaling fast and using tech to improve care delivery while reducing waste across a traditionally paper-heavy industry.
Schedule
- Full-time, remote
- Fast-paced environment with rare needs to work beyond standard hours
- Compensation: $90K–$125K
What You’ll Do
- Partner with Product Engineering, Client Experience, and AI Engineering to identify and resolve issues across multiple products
- Meet virtually with customers and internal teams to diagnose and clarify problems
- Reproduce bugs and troubleshoot issues in production and development environments
- Perform root cause analysis and document findings clearly
- Write detailed technical specs so product engineers can reproduce and resolve issues quickly
- Write scripts and database queries to resolve issues and handle stakeholder requests
What You Need
- 3+ years as a Support Engineer or Software Developer with customer-facing responsibilities
- Working knowledge of MySQL (or Postgres, MSSQL, etc.) and strong querying ability
- Ability to read and write code in at least one modern programming language
- Comfort using Chrome DevTools (or equivalent) to investigate web app issues
- Proven experience debugging complex API integrations
- Strong communication skills, including with senior leadership
- Strong time management and prioritization skills
Benefits
- Competitive salary
- Remote/hybrid environment
- Potential equity compensation for outstanding performance
- Flexible PTO
- Medical, dental, and vision insurance
- Company-paid disability and life insurance
- Company-paid family and medical leave
- 401(k)
- FSA/DCA and commuter benefits
- Discounted pet insurance
- Credits for online fitness classes and gym memberships
- Company-wide sponsored lunches
- Recovery suite at HQ (cold plunge, sauna, shower)
If you’re not comfortable being “on the hook” for high-priority issues and translating them into action across teams, this will be a rough ride. If you are, this role makes you extremely valuable fast.
Happy Hunting,
~Two Chicks…
